Resolution of inherently chiral 1,4-2,5-calix[8]bis-crown-4 derivatives by enantioselective HPLC

Tetrahedron Asymmetry

Volumn 8, Issue 8, 1997, Pages 1169-1173

  Caccamese, Salvatore ^a   Principato, Grazia ^a   Geraci, Corrada ^b   Neri, Placido ^b  

^a UNIVERSITY OF CATANIA   (Italy)

^b CNR   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

CALIXARENE;

ARTICLE; CHIRALITY; CIRCULAR DICHROISM; DRUG PURIFICATION; ENANTIOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IN VITRO STUDY; METHODOLOGY; PRIORITY JOURNAL;

EID: 0030944479     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00115-8     Document Type: Article

References (24)

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2. Gutsche, C. D. Calixarenes; Royal Society of Chemistry: Cambridge, 1989. Calixarenes: A Versatile Class of Macrocyclic Compounds; Vicens, J.; Böhmer, V., Eds.; Kluwer: Dordrecht, 1991. For an update to 1994 see: Böhmer, V. Angew. Chem., Int. Ed. Engl. 1995, 34, 713.
3. Gutsche, C. D. Calixarenes; Royal Society of Chemistry: Cambridge, 1989. Calixarenes: A Versatile Class of Macrocyclic Compounds; Vicens, J.; Böhmer, V., Eds.; Kluwer: Dordrecht, 1991. For an update to 1994 see: Böhmer, V. Angew. Chem., Int. Ed. Engl. 1995, 34, 713.
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6. For more recent examples see: Gonzalez, J. J.; Nieto, P. M.; Prados, P.; Echavarren, A. M.; de Mendoza, J. J. Org. Chem. 1995, 60, 7419. Verboom, W.; Bodewes, P. J.; van Essen, G.; Timmerman, P.; van Hummel, G. J.; Harkema, S.; Reinhoudt, D. N. Tetrahedron 1995, 51, 499. Pappalardo, S.; Parisi, M. F. Tetrahedron Lett. 1996, 37, 1493. Arnecke, R.; Böhmer, V.; Ferguson, G.; Pappalardo, S. Tetrahedron Lett. 1996, 37, 1497. Fu, D.-K; Xu, B.; Swager, T. M. J. Org. Chem. 1996, 61, 802.
7. For more recent examples see: Gonzalez, J. J.; Nieto, P. M.; Prados, P.; Echavarren, A. M.; de Mendoza, J. J. Org. Chem. 1995, 60, 7419. Verboom, W.; Bodewes, P. J.; van Essen, G.; Timmerman, P.; van Hummel, G. J.; Harkema, S.; Reinhoudt, D. N. Tetrahedron 1995, 51, 499. Pappalardo, S.; Parisi, M. F. Tetrahedron Lett. 1996, 37, 1493. Arnecke, R.; Böhmer, V.; Ferguson, G.; Pappalardo, S. Tetrahedron Lett. 1996, 37, 1497. Fu, D.-K; Xu, B.; Swager, T. M. J. Org. Chem. 1996, 61, 802.
8. For more recent examples see: Gonzalez, J. J.; Nieto, P. M.; Prados, P.; Echavarren, A. M.; de Mendoza, J. J. Org. Chem. 1995, 60, 7419. Verboom, W.; Bodewes, P. J.; van Essen, G.; Timmerman, P.; van Hummel, G. J.; Harkema, S.; Reinhoudt, D. N. Tetrahedron 1995, 51, 499. Pappalardo, S.; Parisi, M. F. Tetrahedron Lett. 1996, 37, 1493. Arnecke, R.; Böhmer, V.; Ferguson, G.; Pappalardo, S. Tetrahedron Lett. 1996, 37, 1497. Fu, D.-K; Xu, B.; Swager, T. M. J. Org. Chem. 1996, 61, 802.
9. For more recent examples see: Gonzalez, J. J.; Nieto, P. M.; Prados, P.; Echavarren, A. M.; de Mendoza, J. J. Org. Chem. 1995, 60, 7419. Verboom, W.; Bodewes, P. J.; van Essen, G.; Timmerman, P.; van Hummel, G. J.; Harkema, S.; Reinhoudt, D. N. Tetrahedron 1995, 51, 499. Pappalardo, S.; Parisi, M. F. Tetrahedron Lett. 1996, 37, 1493. Arnecke, R.; Böhmer, V.; Ferguson, G.; Pappalardo, S. Tetrahedron Lett. 1996, 37, 1497. Fu, D.-K; Xu, B.; Swager, T. M. J. Org. Chem. 1996, 61, 802.
10. (a) Pappalardo, S.; Caccamese, S.; Giunta, L. Tetrahedron Lett. 1991, 32, 7747.
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17. 3, 3H), 6.79 and 7.11 (AB, J=2.0 Hz, ArH, 2H), 6.88 (d, J=2.0 Hz, ArH, 1H), 6.90 and 7.09 (AB, J=2.0 Hz, ArH, 2H), 7.10 and 7.21 (AB, J=2.1 Hz, ArH, 2H), 6.91-7.26 (m, ArH, 9H), 7.57, 8.01 (s, OH, 1H, 2H).
18. 10
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20. (b) Vogt, U.; Zugenmaier, P. presented at the European Science Foundation Workshop on Specific Interactions in Polysaccharide Systems, Uppsala, 1983.
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22. Yashima, E.; Okamoto, Y. Bull. Chem. Soc. Jpn. 1995, 68, 3289. Okamoto, Y.; Kaido, Y. J. Chromatogr. 1994, 666, 403.
23. Similar results showing how hydrogen bonding with CSP plays a major role in the chiral recognition process were previously reported for tri-O-alkylated calix[4]arenes (ref 4b).
24. This splitting is observed only at low temperatures (260-250 K) immediately after the addition of Pirkle's reagent (see Figure 2 in ref 6), but can also be obtained at rt after standing at +4°C for 72 h.